Fluorescence and CD spectroscopic sugar sensing by a cyanine-appended diboronic acid probe

被引：66

作者：

Takeuchi, M ^{[1
]}

Mizuno, T ^{[1
]}

Shinmori, H ^{[1
]}

Nakashima, M ^{[1
]}

Shinkai, S ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC ENGN,DEPT CHEM SCI & TECHNOL,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 04期

关键词：

D O I：

10.1016/0040-4020(95)00979-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cyanine dye (4) bearing two boronic acids was designed and synthesized, expecting the selective binding of monosaccharides through the formation of 1:1 intramolecular complexes. While it aggregates in water, it exists discretely in water/methanol 1:1 mixed solvent. In the latter solvent the fluorescence spectra were scarcely affected by the medium pH but efficiently increased when it formed intramolecular 1:1 complexes with monosaccharides. This complexation mode was also corroborated by CD spectroscopy and continuous variation plots. Hence, the saccharide induced fluorescence increase is rationalized in terms of ''rigidification'' of the cyanine skeleton. The association constants (K) were estimated from plots of saccharide concentration vs. fluorescence intensity: the largest K was observed for D-fructose (1.3 x 10(5) M(-1)) and the next for D-arabinose (1.0 x 10(4) M(-1)). This is a novel system for sensitive and selective fluorescence detection of monosaccharides.

引用

页码：1195 / 1204

页数：10

共 38 条

[1] POLAR HOST GUEST INTERACTION - BINDING OF NONIONIC POLAR COMPOUNDS WITH A RESORCINOL-ALDEHYDE CYCLOOLIGOMER AS A LIPOPHILIC POLAR HOST [J].